Roy 'Pretty Boy' Shaw

Roy Shaw served time in Wandsworth prison with the train robber Ronnie Biggs who offered him the chance to escape over the wall. He declined. Photograph: Alamy

The bare-knuckle fighter and armed robber Roy "Pretty Boy" Shaw, who has died aged 76, once gloried in the title of the "hardest man in Britain". The opening line of his 1999 autobiography, Pretty Boy, encapsulates the way that he presented himself to the world: "I am a ruthless bastard."

Born in Stepney, east London, three years before the outbreak of the second world war, Shaw was bullied as a boy and, after his father's death when Shaw was 10, finally reacted to being harassed by lashing out violently. "God had given me a gift," he recalled in Pretty Boy, which was ghosted by Kate Kray, widow of the gangster Ronnie Kray. By 16, Shaw was a schoolboy boxing champion, winning the first of his titles at the Royal Albert Hall.

His first job was in a women's dress factory before he found work in a timber yard in Canning Town, east London. His national service was spent partly in Colchester army prison for attacking staff sergeants and partly in a psychiatric hospital, in Germany, where he was subjected to electroconvulsive therapy (ECT) after a violent fight in a bar. He was given a dishonourable discharge.

Sent to Borstal for the violent robbery of a bookie, he escaped by attacking and stealing the Borstal doctor's car and embarked briefly on a boxing career. He fought professionally under the name of Roy West because he was on the run. Any hopes of a mainstream career in the ring ended, however, when he was rearrested and jailed for a further three years for his attack on the doctor whose car he had stolen.

In 1963, he was a member of a gang that robbed a security van in Kent, for which he was arrested a few weeks later and jailed for 18 years. In Wandsworth prison, he found himself serving time with the train robber Ronnie Biggs, who offered him the chance to escape over the wall if he was prepared to put in £10,000 to cover its costs. He declined because he did not reckon he would have enough money to survive on the outside. In the event, Shaw had already been moved to Parkhurst when Biggs's escape took place in 1965. He kept in touch with Biggs and visited him in Rio de Janeiro years later when Biggs was still on the run.

From Parkhurst, after many violent incidents and clashes with the authorities, he was sent to the psychiatric unit at Grendon Underwood. What he described as his "uncontrollable temper" soon took him to Broadmoor high-security psychiatric hospital. During his five years there, he was injected with a variety of different drugs in a bid to pacify him and made a roof-top protest during which he sang the song Up on the Roof, before he came down.

He was returned to prison and spent the remainder of his sentences in a variety of jails where he channelled his energy into working out with weights. After his eventual release, he was encouraged to try his hand at bare-knuckle fighting and it was through unlicensed contests, with and without gloves, that he established his reputation.

The "Pretty Boy" nickname was the suggestion of a Sun journalist and he also fought under the title of "the Mean Machine".

What was billed as the "fight of the century" and "a fight to the death" between him and the Gypsy boxer Donny "The Bull" Adams, in 1975, was halted by the police on the grounds that such contests were illegal. It attracted enormous publicity at the time and so great was the amount of money riding on it that they agreed to wear gloves and fight. Shaw won and went on to take on his great rival, Lenny "The Guv'nor" McLean, whom he beat. He lost the re-match and a third unlicensed fight with McLean, although the two men continued to differ as to how many times they had actually fought.

After giving up his fighting career, Shaw went into the property business. A second volume of memoirs, Roy Shaw Unleashed, also ghostwritten by Kate Kray, was published in 2003 and footage of his fights found a new audience on YouTube. There are some elements of regret in his memoirs. "It's not big and it's not clever to go to prison," he concluded.